An Escort's Journal
Chapter 1: First-timers
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First-Timers.
Dear Journal,
I awoke this morning to the tinny ring of my cheap alarm clock hammering at my senses, shaking me from slumber with its angry shriek. In a semi-conscious daze I managed to get my hoof onto the switch, and rolled myself out of bed, my bed to be precise not the bed. I blearily searched my small, sparsely furnished room. No decorations colored the walls here, not in this room. This room was my vacation from the rest of my life, and certainly the rest of my house. All that was in here was a single bed, one dresser, and a bedside table topped with my two-bit alarm clock.
I trudged over to my dresser, still barely awake, and let my hooves find my reading glasses. I popped them and grabbed my small black appointment ledger. The cover bore no title or image, only black pleather and little gold corners. With practiced ease I flipped over to today. An appointment awaited me: 3 o’ clock, anonymous. “Terrific,” I groaned to myself “another first-timer.”
First-times usually make anonymous appointments. Sometimes it’s because they’re not sure if they want to go through with it, and leave themselves a little safety barrier. Other times, they just prefer I know as little about them as possible.
I remember, when I received this particular appointment. I found the letter in my mailbox, free of any address, stamp, or name. The letter itself, on the other hoof, was positively loaded with ink. There was a lot of “If it isn't too much trouble” and “If you please”s and endless formality within.
I shook my head, rattling free the negative thoughts in my brain as best I could. It would do no good to head into a meeting with a brand new client with a head full of preconceptions. That’s a good way to lose perfectly good business. I trotted down the hall toward the bathroom. There was much personal maintenance to be done. I examined my reflection in the full body mirror that sat across from my shower. My fetlocks needed to be shorn, my hooves filed a bit, my mane was... fine... for now, but a trim would be needed soon. My coat, definitely needed a good brushing, and lastly, my scruff needed to be shaved.
I sighed, dreading the ordeal. Most ponies would find it silly, going through all this self-beautifying hassle. But hey, no one wants to make a second appointment with a slovenly, unkempt pony; and I’d be damned if I let myself lose a single precious customer just because I was too tired to shave that morning. Not that some ponies don’t like a little scruff; I just like to make a good, clean first impression.
I stepped into my shower, big enough for two ponies, and turned the cold valve. I read somewhere that cold showers are good for you, they help with circulation, help you wake up, and shivering helps burn calories, apparently. All I was thinking about, however, was how much I desperately wished that I did not know that, so that I might have continued to take nice, pleasant, warm showers in blissful ignorance.
After the rather lengthy procedure of getting myself (and the bathroom) neat and tidy, I took a glance examined my reflection once more, to see the face and body that my clients expect of me. Handsome devil.
I made my way downstairs into the main room of my two story cottage, and began my routine inspection, to make sure nothing was even an inch out of place. Two large, comfortable cushions sat opposite each other, sandwiching a small wooden table complete with two white tea cups, and a tea kettle atop a decorative trivet. Across the room from the small arrangement stood my fireplace, a small marble hearth decorated with ivy (the plastic kind) and filled with enough wood to get a roaring fire burning. The rest of the room was dotted with carefully placed decorative throw pillows and candles. Everything was absolutely perfect.
I grinned to myself, and walked into my kitchenette to make some breakfast. I poured myself a nice big bowl of breakfast cereal. I know that a guy who takes as much care of his body as I do probably shouldn't start the day with something almost entirely marshmallows, but hey who’s perfect. I happily chewed into the sugary blobs. A glance at the clock told me that this was, in fact, lunch; because 2:30 was far too late for breakfast. 'Wait a second, 2:30?'
“Shit.” I quietly swore, as I began to wolf down my cereal like a prison inmate. I had only 30 minutes to finish my breakf… lunch, tidy the kitchen, and get dressed. I know a lot of ponies talk about getting dressed like it’s easy, and there is a very good reason for them to believe that.
They are unicorns.
I would like to make something perfectly clear, putting on clothes without the telekinetic aid of magic is, and pardon my language, a fucking chore. Hooves and mouth alone make the task of changing pretty difficult. Even wings would be nice, I've seen pegasi use those babies with amazing levels or precision, if fact just two weeks ago a lovely client… never mind.
Now, while I’m fully aware that it’s socially acceptable to not wear clothes in public, especially in this rural setting, I like to wear clothes. I’m from Manehattan, and a lot more ponies wear clothes there. That, and I feel that the addition of jeans to my image makes me a bit more mysterious; mystery gets ponies talking, which gets them interested.
Where was I? Oh yes, getting dressed. After I wriggled my way into my signature blue jeans, (a task I feel I have adequately covered the difficulty of,) I made my way back downstairs with only moments to spare. I watched the large clock in the main room tick over to 3 o’ clock. Right as I was about to sit myself down onto one of the green cushions, there was a faint knock at the door. That’s another first-timer habit, they always knock quietly, hoping I won’t hear, so they can just turn around and say ‘oh well, guess he’s not home.’
I quickly jogged to the door, and prepared my act. My eyes half lidded themselves into a sultry gaze, my face plastered itself into my practiced ‘pleasant grin,’ and I cleared my throat, preparing for what could potentially be hours of suave baritone.
Okay, maybe it’s more of a tenor.
I slid open the door coming face to face with my client. She was purple, lavender really, her mane a sort of deep indigo. A duo of stripes, pink and purple ran down one side of her bangs, just past her horn. Her face was a mix of nervous and embarrassed; she was blushing almost up to her ears. The moment her gaze met mine it shot to her hooves, which raked nervously against the brick stoop of my home. She was adorable.
“H-H-Hi…” was all she managed to get out before an almost tangible wave of embarrassment swelled up her face.
“Hello, miss.” My voice slid into its sultry cadence, if only just so. This wasn't the time to lay it on thick. “Please, come in…” I slid back, as she stepped into my home. As she walked past, I caught a glimpse of her cutie mark: a pink starburst fringed with smaller white stars. An astronomer maybe? “Take a seat, please, and I’ll put the kettle on.” She obliged, legs folding under her as she got comfortable on a cushion. I grabbed the kettle and trotted off to my little kitchenette. I like to take my time when I do this, give the client a chance to acclimate, take in the surroundings. It puts them at ease.
After a few minutes, I returned, and took the seat opposite her. “Do you have a preference for tea? I've got quite a selection,” I recited.
Her words came as a whirlwind, flying out of her mouth in nervous flurries. “Oh none for me thanks, I think right now stimulants would only exacerbate my already tremendous amounts of nervous energy!” She stated very matter-of-factly despite her panic. Big on words, this one.
I stopped myself from rolling my eyes. I tried to meet her gaze only to find hers staring dead at my table. “I should say so.” I chuckled. “Well, let’s get started shall we?”
“Oh, right now? As in, right now right now?” Her eyes began to dart every which way around the room. “Because I’m not ready, I mean I only just got here and I thought I’d have a few minutes or so to prepare myself and...”
“Calm down.” I cut her off as gently as I could. “I only meant let’s get started talking, there’s some things to discuss before we do anything.” I put on a reassuring smile, and she relaxed a bit. “Firstly, I have a question.” She gulped; she didn't know what to expect. First-timers never do. “What should I call you? You can use your name, or anything, really. But I can’t go around calling you ‘you,’ now can I?”
She blinked, and her hoof met her chin in contemplation. She pondered for a while. A less-experienced pony of my profession might be tempted to hurry her along, but two very important facts keep me from ever rushing a client. First, in my line of work you never want to rush anypony, this is the sort of thing that needs to be done at their pace. Second, I’m hourly, why would I ever hurry anything?
She finally spoke up, looking me straight in the eye for the first time. “My name is Twilight.” She said, with only slight waver in her voice. She smiled nervously.
“Very well,” I smiled back at her. “It’s a pleasure to meet you Twilight. Now there are a few more questions I’d like to ask, if that’s alright.” She nodded. “Firstly there’s the matter of *ahem*…” I adjusted my position slightly to appear nervous. I wasn't really nervous, but seeing me a little nervous tends to calm ponies down. It’s all part of the act. “…payment. You never mentioned in your letter how much time you were planning on spending here.”
“Oh!” she piped up, her voice the calmest I’d heard it yet. “I didn't think of that.” She pondered once more. “Um… how long do ponies usually take to… I mean, do you charge just for the time when you’re…” she trailed off, as her blush crept back into her face.
“I start charging from the moment you walk in the door, and I stop charging when you leave. I’m sorry if there was any confusion.” I adjusted myself again, okay, maybe I was nervous. I never like telling ponies they owe me money. ‘But hey business is business,’ I told myself. “My price will be 20 bits an hour, starting from 3 o’ clock.”
“Oh… okay um… I guess I’ll pay for 3 hours. What happens if I run over?” Her nervousness was picking back up. I had to rein her in fast, or this mare was going to escalate into full meltdown.
“How about I just collect at the end, and charge you for the time you used, sound good?”
“O-Okay, that sounds fine.” Her bout of nerves passed; and she began to glance about the room. “You have a lovely home, must be nice living here… but it’s so far from Ponyville.” Finally, she was easing into casual conversation.
“Well, thank you, I do love living here…” Well, not here here, I live upstairs, but she didn't need to know that. “And as for it being far, that’s... uh... not really by choice. There are a number of ponies who prefer that my... entrepreneurial escapades, shall we say, be kept far out of Ponyville proper.”
“Really? Why?” She inquired, genuinely curious.
“Well I’m sure it’s just because many ponies don’t agree with my profession. But the official reason is so that no children accidentally wander in and be horribly traumatized, or something along those lines.” I concluded with a sigh. “Well enough about me, I’m more interested in you.” I playfully smirked. “One thing I’m curious about. How did you hear about me?”
I took a moment for her to realize I was asking her a question, until she gasped in realization. “Oh, um, from a friend.” She grinned wide, hoping that would suffice.
“Everypony knows everypony in Ponyville.” I smirked right back. I made a small bridge with my hooves and delicately rested my chin on them. “I want to know which friend. If you don’t want to tell me their name, that’s fine, but could you maybe describe them.”
Her eyes closed, and she took a deep breath. “Her name is Rarity.” She said with calm resolve. This mare was proving to be a lot more confident than I took her for.
“Oh, Rarity?” I couldn't help but laugh. Close to half of my clientele is referred by her.
“What’s so funny?” There was a sort of innocent curiosity about the way she said that.
“Oh, I just get a lot of clients from her.” I reined in my outburst. “Well, all that’s left is the big question.” She gulped. “What can I…” I motioned toward myself with a hoof and swung it around to point at her “…do for you?” Normally I would lay it on thick with my 'what-I-really-wish-was-low-enough-to-be-baritone,’ but something told me that this unicorn is just a little too smart for that, so instead I adopted a tone similar to her own, one of genuine inquiry and wonder. I did my best to appear curious.
“Oh well…” She swallowed hard again. Just as she opened her mouth to speak again, the air began to fill with the rising whistle of the tea kettle.
“Hold that thought.” I raised myself off the cushion and cantered into the kitchen. I quickly scooped a half-measure of tea leaves into the kettle. As I stepped back into the living room, kettle in mouth, I came to a sudden realization. 'Oh, HAY, I forgot to put on music.' One thing you learn in my profession, is that if things are going well, you don’t go out of your way to change them. Now, music serves a number of purposes, it’s a conversation topic, and the right music can certainly set the right mood, but above all, music makes the awkward silences that much less awkward, which is why, it really sucked that I didn't have any. The issue was, if I started the music then, it would have looked like I was trying to set up a certain mood, much more so than if it had been playing from the beginning. Clients, new clients especially, hate feeling like they’re being nudged into anything. Even the mares who like being tied up need to be in control.
But hey I’m a perfectionist, things were probably going to be fine… probably.
I returned to the table, placing the kettle on the trivet. I sat back down on my little cushion. “I made it a bit weak just in case you wanted some.”
“Oh... thanks…” Her face found its way to the table once more. This time it seemed to be depression, not nerves.
“Something wrong?” I inquire.
“No… It’s just… it feels weird… paying for…”
“You, Miss Twilight, are paying for somepony's valuable time and nothing more.” I cut her off. I really wasn't planning on doing that, but this is a point of pride for me. “As a matter of fact, I have had a number of jobs wherein my client and I only chatted.” I announced proudly. It wasn't exactly a large number, but it was a number.
“You mean… we don’t have to have sex?” I just shook my head and smiled.
“Well that certainly simplifies things.” She gave a relieved sigh.
My face became one of confusion. “Well I guess that brings me back to my question… what can I do for you, Miss Twilight?”
She reddened again, but only slightly. “Well, Mister… Oh my gosh.” Her pupils shrank. “I... I don’t even know your name!” ‘She’s about to start freaking out again, isn't she.’ “Oh my gosh, and I call myself a student of friendship?! Some friend I am…” ‘Yes, Yes she is.’ She stood up, and began pacing about the room in a nervous tizzy ranting to herself about being sent to the moon or something. I knew I had to stop this nervousness once and for all.
I walked right up to her and looked her in the eyes. “My name…” My voice was even and low. Her gaze snapped to meet mine, tears starting to form in her eyes, and breath heavy with panic. “… is Guilty Pleasure, and I am an Escort. It is my job to make you happy, and to be your friend. You cannot disappoint me, you cannot offend me, and I will never ever judge you for anything you say or do in this house.” Her face became one of contented calm, hopefully for good this time. “So don’t worry so much.” I threw on my very best, ‘I understand, everything is going to be okay, award winning, hunky smile.’ She just stared up at me, for a bit, almost in awe. She opened her mouth to speak, I expected something along the lines of ‘thank you for being so understanding, you've really put me at ease.’
“I wanna watch you masturbate.” she said bluntly.
“Um… okay.” I was not prepared for that. “any particular reason? Not that I mind... at all!” I stammered. That one had taken me off guard.
“Well…” her whole temperament had pulled a 180°, and suddenly she was acting like she’d been coming here for years. “… I met this Stallion, and he’s really nice. I haven’t asked him out yet, but I want to. The thing is, I've never had… any real contact with the opposite sex.” She took her seat once again and magically poured herself a cup of tea, and a cup for me as well. Her magic had a beautiful hue to it, purple and pink, almost like the stripes that ran through her mane.
I sat opposite her once more. “Go on.” Finally I was getting somewhere.
“Well I was talking with Rarity…” She took a swig from her cup “… oh wow that really is weak.” She interrupted herself, scowling at her cup. “Anyways, Rarity said that I should just go for it and ask him out. So I said, I wasn't sure and I’d never dated a guy, and we got to talking and she kind of helped me figure out why I was so nervous about it. I’d never even seen a guy’s thingy before.” ‘Thingy... adorable’ She finished off her cup, and set it down. “So Rarity told me about you, and what you do. She said you were well-mannered and considerate.”
“Well I like to think I am.” I harrumphed softly and took a sip from my own cup. She was right it was far too weak, even if I had meant it. “So if I understand this, you want to ask a guy out, but not without understanding his... biology? Can I ask why? Are you planning on going that far on the first date?” I took another sip. “Not that that’s bad or anything.” I hastily added.
“Well, I guess I was, I mean... if he wants to and everything.” She murmured.
“Not that it’s really my place, Miss Twilight…”
“Please…” She smiled “Just Twilight.”
I grinned back at her, I take a certain pride in getting a client comfortable enough to be casual. “Certainly, Twilight, but if I may...” She nodded. “You should not be having sex before you are ready.”
“But what if he wants to?” she inquired.
“Simple…” I stated “Say ‘no.’”
“I couldn't do that, what if he never talks to me again because of that!?” She sounded almost angry at me for even suggesting such an outrageous course of action.
“Then he was never worth your time to begin with,” I say flatly. “Trust me.” She seemed to accept that. After only a moment, she stood up, “Okay then, Now w-w-why don’t we get those pants off of you.” She was blushing again, but she wasn't letting her embarrassment stop her.
I snickered like a schoolfilly, hearing her say that so nervously. I led her to the door opposite the kitchen, and into the bedroom, HER bedroom, not MY bedroom.
Stepping into the bedroom is quite an experience, especially for a first timer. Large trunks sit in various arrangements about the room, housing all manner of naughty apparatus, from ropes and handcuffs, to edible socks, to some stuff that I’m still not sure are even meant for ponies. Tall shelves line half of the walls, lined with potions and oils, books and scrolls. And, of course. what bedroom is complete without a bed.
The bed is easily the most expensive thing I own; perfectly round and free of any sort of headboard. The pillows are filled with real phoenix down; the comforter is stuffed with golden wool. But the mattress is where it really shines, a simple sheet wrapped around an enchanted cloud, the most comfortable thing I've ever had the pleasure of sleeping on.
Twilight, on the other hoof, was much more interested in the books. “ I've never even heard of half of these. Where did you get them?” She asked, stepping over to a rather sizable bookshelf. Her magic slid a small scroll off the shelf, and she began to peruse its rather graphic imagery, a blush once more creeping into her face, more from arousal than embarrassment, I assumed.
I trotted over to a smaller trunk, and pulled out a long fragrant stick of incense and a book of matches. “A lot are from a little antique shop I used to live near in Manehattan. Over the years I built up quite a collection.” I slid the lavender stick into a small holder beside the bed. “That’s a translated copy of the Camel Sutra, unabridged, by the way. Would you mind lighting this?” I indicated the incense.
“Huh? Oh, sure, no problem.” She quickly rolled the scroll up tightly, and magicked it back to its spot on the shelf. With a quick flash of her horn, the incense was suddenly lit, its pale smoke, wafting into the air and into my nostrils.
“Wow, so is that your special talent? Fire, I mean? I was just going to ask you to use one of these.” I briefly regarded the matchbook.
“Oh, no no no.” She turned, putting her cutie mark on display just for me. “My special talent is magic.” She smiled to herself, bringing a hoof to her chest in triumph.
Absolutely. Adorable.
“I didn't know magic could be a unicorn’s special talent. Wouldn't that just make you good at… everything?” I half asked half joked.
She scratched the back of her neck with a hoof. “Well I don’t like to brag or anything… oh WOW that smells good.” She regarded the smoldering stick of lavender just as a single burning cherry of ash fell onto the decorative wooden holder.
“I’m glad you like it, and if you’d like to borrow any of those books, just ask, I’ll let you know.” I grinned. I was actually enjoying talking to this mare; She was fairly comfortable with me for a first-timer.
“Thanks, but that might not be the best idea.” She sounded a little disappointed. “I would really love to, but I kind of… live with a kid a little young for that kind of stuff, and I’d really hate for him to stumble across it.” She sighed heavily. She clearly wanted to take something with her. An idea popped into my head right then, but I decided to give voice to it later, and see if I couldn't get some repeat business from this mare. But right now, I figured it was about time to get down to the deed.
“So shall we begin?” I queried, flopping down on my bed made of pure heaven.
“No time like the present.” She said, a smile almost free of worry adorning her face. Her magic rather suddenly extracted a pad of paper and pencil from her mane. “Do you mind if I take notes?”
I smiled back, and began to undo the button on my jeans. I could already feel myself hardening. “Go right on ahead, Twilight.” I giggled, delighting in her cute innocence once more. Fortunately for me, Undressing takes much less time than actually dressing. With a few careful motions, I slid my jeans down around my fetlocks, and playfully kicked them away. I looked back to Twilight. Her face was... confused. I wondered briefly precisely what she was expecting, until I noticed that her gaze was not directed toward my semi-firm stallionhood, but rather my flank. “Your cutie mark is a book?!” She almost yelled.
“Huh? Oh... Yes, yes it is.” Everyone asks that eventually, I just thought the little lavender mare might have more pressing priorities, like the ever expanding organ between my hind legs. “You want me to do this or…”
“What? Oh, yes of course, I just… a book?” She said perplexedly, “It just seems so…” she mused. “It doesn't fit. Wait, what is your special talent? I just assumed it was…. you know.” Her ears went flat as a sad ache crept into her voice.
‘Great, now she’s angry at herself for making assumptions… she REALLY needs to lighten up… Let’s see if I can’t distract her.’ I punctuated my interior monologue with a mischievous grin. I spread my legs wide toward her, as she looked despondently at the floor. “Twilight,” I softly called her name, adopting my ‘bedroom voice.’ Her eyes turned to me and immediately caught sight my now fully erect self. Her blush rocketed to new levels, turning even the tips of her ears red.
“Wow…” she mumbled. Her eyes transfixed on my stallionhood. “I knew they were supposed to get bigger but… oh my gosh.” Her hover pencil began scribbling furiously, but her attention seemed to be entirely on me.
“Just so you know…” I said, shifting my shoulders into a slightly more comfortable lean. “I’m actually a little on the small side.” I let hoof find its way up my shaft, gently tickling its sensitive surface.
“That’s… terrifying to think about,” she pondered. I fell into a rhythm of gently stroking myself, My skin stretching slightly with each pump. I watched Twilight as she stared at my little performance, her hips ever so slightly twitching as she stood, her tail slowly raising itself. Sadly from my position, I had no view of the sopping prize beneath. Her pencil and notepad scribbled furiously seemingly of their own accord.
I stopped my movements as I felt myself beginning to crest. As good with my hooves as I am, It certainly doesn’t take me that long to get people I’ve never met off, much less myself, and I felt no reason to end Twilight’s little show so soon. I raised myself from the bed and began to walk past Twilight over to one of the shelves across the room. I made sure to raise my tail, just enough to make myself visible, should she decide to turn around and catch a glimpse. I snatched a bottle off of the shelf, and turned back to the bed, Twilight’s face asked the obvious question before her lips even could.
“What’s that?” came her inquiry, eyes locked on something other than my cock.
“It’s honey-lemon oil. It’s my favorite.” I smiled as I appreciated the small, half-full carafe of pale yellow fluid. “It smells absolutely wonderful, especially with the lavender.” I grabbed the small glass stopper in my teeth as I took my spot on the bed once more. I poured a small dribble of the fluid onto my free hoof, and bent myself down to place the bottle on the floor.
My newly oiled hoof took a firm grasp of my flesh and began pumping with renewed vigor. The familiar warming sensation of the oil seeped its way into me as the delicious honey-lavender -lemon smell permeated the air. After minutes of grunting and the slapping noises of wet flesh, I felt myself approaching the point of no return.
“I’m going to finish soon,” I breathed. “Where do you want it?” My hoof began to stroke faster than ever.
“Want what?” I imagine she would have reddened further if such a thing were possible.
“My come, Twilight. Where do you want me to come?” I managed to hold myself off long enough to make sure I had time to hear her answer.
“I don’t know… anywhere!” she shouted, her voice fraught with alarm and confusion.
‘I may as well give her a show.’ I took hold of myself, and aimed upwards across the room. Climax filled my senses as my testes clenched tight, and ribbons of sticky jism cascaded a short way across the room. The spent seed splattered unceremoniously onto the wooden floor a yard away from my seat, and the only sound that filled the room was my blissful panting. I collapsed against the bed, forelegs sore and breath heavy. It took some effort to even speak.
“That… *huff*…*huff*… felt good.” I laughed heartily as I sat myself up. “I really should do that more often.” I cast a lazy glance at Twilight, who appeared to be stunned into silence, staring at the sticky clear splotches on the floor, her pencil and paper dead in the air. “So what did you think?”
“That…” she continued to stare at the floor “… was interesting.” She looked back to face me; her hovering notepad snapped shut, and quickly found its way back into her mane. Her expression was... troubled? She noticed my look of concern. “I don’t know it all just seems very… hard?”
“Well it does tend to get pretty firm…,” I teased. She glared at me a bit. “…but that’s not what you meant.” I did my best to be supportive, and help her sort out all the new information she’d learned. “Sex can be… exhausting, but it’s really worth it. At least in my opinion it is.” I stood myself up, and stepped over to another chest in the corner of the room. I picked a white towel out of it and walked over to the mess I’d left on a large portion of my floor.
“Worth it how? It seems like a whole lot of work, for only a few moments of payoff.” She looked skeptical, and that look caused something to suddenly click for me.
“Oh my gosh, you've never had an orgasm have you?” I asked without thinking, as I began to meticulously wipe my spunk off of the hard wood.
“What?! Of course not! I've never had sex!” She looked almost hurt, as though I’d made some terrible accusation against her personage.
“Well we didn't have sex, and I just came.” I offered, confident she’d pick up the implication.
“But I've never… how could I… It’s so… girls don’t do that!” She was on the defensive yet again… something was really eating at her, I could tell.
“Twilight, I have extensive firsthand experience, that tells me that girls can, and do, masturbate…” I countered. I finished wiping up, only to notice another mess on the floor, a mess that did not belong to me. “…and by the looks of things you could really afford to rub one out, as well.” I regarded a small clear puddle on the floor, directly beneath where Twilight’s hind legs.
Twilight followed my gaze, and twisted her face into one of shocked horror, as she realized precisely what she was looking at.
“Oh no no no no no no…” she frantically shook her head. “I don’t… I know I’m not going to have sex so why…?”
“Because you’re aroused,” I stated. “It happens.”
“But it’s not supposed to just happen!” she looked pleadingly in my eyes, wanting me to somehow make it better, to make everything okay. So, that’s exactly what I did.
“Twilight, you don’t think you’re capable of controlling when you’re aroused do you? Because If anyone in all of Ponyville could do that, It would be me. With all my experience, all of my practice, and all of my sheer force of will... I still get stiffies when I don’t want them.” I walked up and placed my hoof… my clean hoof… on her shoulder. “There’s no shame in being horny for no reason.”
“You’re sure?” She had tears in her eyes now, I only saw them briefly before her face was thrust into my shoulder, and she began bawling. I had figured something out about poor Twilight. She had thought she was a ‘bad girl’ for getting aroused, and without an outlet she only got more and more horny, which in turn only made her feel worse and worse. It was tragic... adorably tragic... but tragic.
Her head pulled away from my shoulder as bawling gave way to sobs, which in turn gave way to quiet sniffs. “Sorry,” she laughed despite herself, eyes puffy and wet.
“What did I say earlier? No judgment.” I smiled. “Now, how about this. I am going to teach you, Twilight, how to pleasure yourself, because you are in desperate need of a way to blow off some steam.”
“What? But, if all goes well, soon I won’t need to. I mean, If I end up with a boyfriend, why would I need to blow off steam?” She looked at me quizzically. “I always heard that boys want it all the time, so I should be in the clear right?”
I rolled my eyes. “You’d be surprised, I wouldn't be at all shocked if this guy couldn't keep up with you. Even so, sometimes you’ll rather just jerk it than have sex.”
“Okay, but don’t say ‘jerk it.’” she laughed, as I led her to yet another on the chests in my room.
“These, Twilight…” I pause for effect as I lifted the lid, displaying its contents within. Several plastic toys of varying length and girth, arranged in a foam display casing sat inconspicuously in the box. “… are vibrators,” I stated as reassuringly as I could. She immediately began examining one of the larger specimens: a great big, veiny, black monster of a dildo.
“Oh my Gosh, It’s enormous!” She giggled for a while before hovering it back into its slot. She then removed a small pink egg vibrator, and gave the switch an exploratory flip. The little egg hummed to life in the air, and she giggled once more.
“That one is probably more your speed. Come, sit on the bed.” She trotted over to the bed, vibrating egg in telekinetic tow. She tentatively sat the bed, and gave the mattress a scrutinizing.
“This is really comfy, what is it?”
“Uhh, it’s enchanted cumulus,” I explained.
Her eyes went wide. “Wait, you mean this is a cloud, but how come we can touch it? I mean, I know a spell to make a pony walk on clouds, but not one that makes a cloud solid for all ponies. How do they do it?” Her eager smile beamed at me.
I shrugged. “Oh man, heck if I know, I know nothing about magic.”
She prodded the cloud bed with a hoof. “It’s fascinating.”
I chuckled. “I’m glad you like it. Shall we begin?”
She blushed once more, and nodded her head with conviction. She gulped audibly. “Um we can start but, I don’t want you to see anything.” She crossed her legs defensively.
‘Damn,’ I lamented internally. “No problem, Twilight, let me just grab a cushion from the living room.” I quickly fetched a cushion and placed it between the bed and the door. I sat, facing away from Twilight. “How’s that?”
“No peaking!” I could practically hear her blush.
“No peaking, Twilight,” I reassured her. “Now let’s do it like this: I’ll direct you from here, and if anything makes you uncomfortable you let me know.”
“O-Okay,” she said.
“Okay, now I want to lie back and take a deep breath.”
“Okay.” I heard the sound of sheets ruffling under her coat, followed by a long heavy breath.
“Now I want you to spreeeaaad your hind legs,” I kept my voice as gentle as I could, scaring this far in could set her back miles.
“O-Okay,” she complied… or at least I assumed she did.
“Is the toy still on?”
“It’s on!” I don’t think she meant to yell, but she was starting to panic.
“Calm down, Twilight, For now I want you to turn it off, can you do that?”
“Sure.” I heard the quiet click of the toys switch being set into an off position.
“Okay, now we’re going to get a little more serious. If you’re comfortable, I want you to take hoof, and reach slowly down between your hind legs.” There was no response this time, but the faint sound of rustling fur told me she had complied. “Now I just want you to touch yourself, don’t try to stimulate yourself yet, just get familiar with the area.” I cleared my throat slightly. “Now one thing I want you to keep in mind is that there is nothing to be ashamed of here. Whether they’re public about it or not, lots of ponies masturbate, and it’s perfectly natural and normal.” I felt a little bit like an X-rated after school special, my speech was a little generic, but it got the point across. “Now if you don’t mind me asking, how do you feel?”
Her response came after a long pause, “It kind of… tickles, I guess. I’m still all w-wet from… you know… watching you.” I could hear her breathing become excited and heavy. “I like it so far.”
“That’s good, now I want you to find something you do that feels especially good, and keep doing it, go as fast and firm as you’re okay with.” An almost soundless schlicking noise started to rise in the room, as well as an occasional blissful whimper. “Feel good?” I asked.
“Y-y-y-yeah,” came her pleasure laden response.
“Now I just want you to keep at it for a while, I’ll be here, just let me know if you need anything, or if something feels wrong.” I figured the odds of that were very low, but anything to comfort my client.
Minutes passed and the pace of her movement began to pick up, and her moans became long and throaty. I could tell she was really getting into it… as was I. I could feel myself getting hard in my seat.
I’ll be honest. I wanted very badly to mount her then and there, to rush over and teach her all kinds of pleasure. That said, I have standards, I was here to help her as best I could with what she wanted, not what I wanted. I was not about to seduce a mare who had plans of asking out some lucky… very lucky… stallion with hopes of starting something meaningful. I’m not the kind of stallion who does that kind of thing… at least not anymore.
Eventually she spoke up, voice panting and drunk on pleasure. “I think… *huff*… I’m ready to try… *huff*… something more… *huff*… advanced.” Her newly broken-in hooves had apparently brought her as close to orgasm as they could at present. I wasn't worried, I was sure that before long, she’d be able to get off with the best of them.
“Okay Twilight, now do you see that bottle of oil from Earlier?” I asked.
Shifting fabric preceded her response. “Yeah.”
“I’d like you to pour a little out onto your hoof, and rub it on the egg.” My own need for satisfaction was becoming unbearable; if I didn't do something about it I was going to lose all sanity. “On an unrelated note, I’d like to ask your permission for something.”
“What is it? Did I do something wrong?”
I answered before she had a chance to panic. “No, Twilight, I just have a request. I’m getting very aroused, and I was wondering if you would mind if I pleasured myself as well.” A response came in the form of the small crystal bottle of oil levitating over to me. ‘She wasn't kidding about her special talent’ I mused ‘that’s quite some range for a pleasure drunk unicorn.’
I doled myself out a small portion of oil and took grip of my stallionhood. A small gasp came from the mare. “This stuff gets warm.”
“Sorry, I should have warned you… does it feel okay?” I really hoped I hadn't messed up with that one.
“Yeah, it’s okay… a little weird, but okay,” she responded. “So now what?”
“I want you to turn on the toy, it’s only got one setting, and put it wherever feels best, a lot of mare like it right at the top of their lips, there’s a little nub…”
“I know what a clitoris is,” she deadpanned. The buzzing of the toy hummed through the silence, when suddenly Twilight let forth a far from quiet moan of ecstacy. “Aaah!” The buzzing continued and I could hear Twilight kicking at the sheets, I could tell this wouldn't take long.
Breathing, kicking, panting, the furious shlicking noises, everything began to escalate to climax, for both her and myself. The smell of wanting mare filled my nostrils and tipped me over the edge. Hot cum sputtered out of me. nowhere near the force of earlier, dribbling out onto my chest and down my ever-shrinking shaft.
Just as the wave of my orgasm began to pass, I could her Twilight’s crest. “AAAAAAAAAOOOOOOHCELESTIATHATFEELSGOOOOOOOOOOOOD!” Her screaming continued for what could easily have been half a minute, until finally I heard her collapse.
I let her stew in her own pleasure for a while, before finally saying something. “So…?”
“Okay... definitely, definitely, definitely, worth it.” I could practically hear her smile.
“Why don’t you collect yourself and we’ll…”
“Oh my gosh... Oh no no no no!”
‘Sweet Luna what is it this time?’ “What happened, are you okay?”
“I’m sorry, I’m sorry, I’m sorry! I just… it felt so good, I….”
“Can I turn around? Are you decent?” I asked, genuinely concerned, I was fairly certain it was no big deal, but she
needed reassuring, or else all of this work could end up bolstering any discomfort with sex.
“I’m decent but don’t turn around!” she shouted.
“What happened?” my voice was nothing but concern and worry. Tone of voice goes a long way, it can make the difference between a pony trusting you or not. I’m very good at getting ponies to trust me.
“Oh, please don’t be mad,” she fretted
“I won’t, now just tell me what happened,” I said, keeping frustration out of my voice completely.
“W-well, when I... um… came,” she whispered that word, “ I kind of… um…” she mumbled something I didn’t quite catch.
“What was that?”
“I… peed… a lot.” Her voice began to once more turn to tears.
“Oh, is that all?” I ask, my voice thick with relief.
“What do you mean is that all!? Something must be wrong with my vagina! How does this kind of thing even happen!?” I heard her hooves tapping the wood as she paced around the room in what had to have been her twentieth nervous tizzy of the evening.
“Well, I can’t attest to precisely how it happens, but I can tell you that it happens all the time,” I informed her.
“R-really?” she asked in hopeful desperation.
“Yes,” I reassured her. “Can I turn around now?”
“I guess.” She finally surrendered, and I turned around to survey the damage, well aware that no matter how bad it was, that I’d play it off like it was nothing. I took a glance at the puddle in the middle of the bed, it was pretty big, but nothing I haven’t seen before.
I let my face relax into one of calm reassurance. I looked to Twilight who stood as small as she could, eyes downcast, rubbing her fetlocks together is shame. “It’s not a big deal, Twilight. It’s not that uncommon.” Her face looked up at mine, the absolute picture of embarrassment. “In fact, It’s so ‘not-uncommon’ it has a name. It’s called ‘Stress Incontinence.’ The short version is that lots of stress, namely stimulation, makes you lose control of your bladder.
Her face began to relax, she seemed to like when I sounded like a textbook. “But, I made such a mess of your bed,” she half-cried, eyes stuck on her shameful splotch.
“Sheets can be washed; and the mattress is a cloud. Everything rains out of it.”
She was quiet for a long time. When I say quiet, I mean she didn't say anything; she was still sobbing a little. “Okay,” she finally managed.
“Now, I’ll worry about this. You’re probably going to want to shower or something; you can use the bathroom upstairs. You saw the stairs when you came in right?” I asked, already hard at work taking the sheets off the bed.
“Yeah,” she answered, clearly happy to have something else to think about.
“First door on the right, you’re welcome to any shampoo or anything in there… I got all kinds.” Twilight nodded, and left the bedroom quietly, still partially ashamed of herself. The smell of urine started to permeate the air as I carried the sheets into the hamper I keep in the closet. I sighed heavily, hopefully after a quick rinse Twilight would come downstairs and be satisfied with my services, and we could discuss future business.
I decided that rather than sit there and twiddle my hooves, a more productive thing to do would be to clean the semen out of my coat, put the cushion back where it belonged, and make some actually tasty tea. After that ordeal I was sure we could both use some. A quick rub down with a wet towel and I was good to go, and after a few minutes of preparation the kettle began to whistle, just as I heard Twilight make her way down the stairs.
‘Here’s the Moment of truth.’ “That has got to be the nicest bathroom I've ever seen. I didn't know anyone even made zap apple Shampoo.” Her smile positively beamed as she trotted past the kitchen. ‘Well, she’s happy at least, that’s a good sign.’
I cleared my throat. “So, Twilight, I must ask… were you happy with our little… show and tell?” I tried my very best not to sound desperate.
She took deep breath and smiled dreamily toward me. “More than happy, Mr. Pleasure, It was… you were… completely perfect.” I fight the urge to pump my hoof wildly. “You taught me so much and I really… I can’t thank you enough.”
“Let’s not go that far. I’m glad I could help, but I’m sure it wasn't that mind-blowing.” I motioned over to the table. “Why don’t we have a cup or two? I promise it’s good this time.”
She tittered as we both made our way to the table. Twilight poured tea into the two cups as we took our seats. “So, would you say you’re all ready to ask out your hopefully-special-somepony?” I took a deep swig of the tea, thankfully it was good.
“I would have to say, Mr. Pleasure, that I believe I am.” Her pride practically poured out of her.
“Please,” I corrected her. “Just Guilty.”
“Okay, Guilty. So, uh…” she glanced curiously at me. “What happens now?” It was her turn to drink, a smiling glance at the tea told me she approved.
“I’m glad you asked. One thing I would like to discuss, if I may be so bold, Is the prospect of repeat business.” I put down my teacup. “I know you plan on seeing someone, but that doesn’t mean your appointments need to stop. If you like, you can always come over for dating advice, should you feel your friends aren’t helping you.” It was time to enact the plan I’d been formulating since she first laid eyes on my collection of antique books. “However one thing I think we’d both enjoy is if got together for study sessions.” Her eyes absolutely lit up at the suggestion. “Well I could tell you liked my books but didn’t really feel safe taking them home, so if you like, we could get together for a little… reading party every so often… does that sound nice?” I finished my proposition, and finished my tea as well.
“That sounds… well, as a certain friend of mine would say… totally awesome.” She regarded her tea thoughtfully. “Orgasms too, they’re also totally awesome.” She polished off her cup as I laughed uproariously.
“I gotta say Twilight, It’s refreshing to have a client like you.” I reached to pour myself a second glass, but Twilight beat me to it, distributing tea into both cups.
“How do you mean?”
“Well…” I pondered a while, and tried to figure out precisely what I meant as well. Eventually I found the words. “Most ponies come to me, and they’re trying to escape. Some just need me for physical satisfaction; some just need someone to whine to. Occasionally ponies come in out of pure boredom, But all of them are just trying to get away from something or someone. But you… you came to me not for escape, but for help. You came to me, looking to better yourself. It’s…” I gazed into her eyes, and for the first time really noticed their hue, a vivid purple, just like the stripe in her mane. “…refreshing.”
She frowned. “That’s a sad way of looking at it.”
“Oh?” I confess I was curious to see where she was going with this.
“Those ponies that come to you… they need help to. They all have problems they need help with. Maybe they are using you as an escape, but maybe that’s what they need: an evening away from their problems, a vacation just for them.”
“Maybe you’re right, Twilight.” I looked at the clock; it read 5:12. Well unless you have anything you’d like to discuss…” I waited to see if she would interrupt me “… then I think we are done here. That was just over two hours, normally once we break into an hour I charge for it, but I’ll make an exception this time.” I winked at her. “So that will come to forty bits, Twilight. I hope you find the price acceptable.”
“That’s perfectly fine, guilty.” A coin purse levitated out of her mane, and forty bits counted itself onto my table.
“How much cool stuff can you fit into that mane?” I ask with a chuckle.
“Oh it’s just a spatial compression spell I've been working on. I've been messing around with the Hoofstein laws of spacial condensing to see if I can’t find a way to…”
“Aaaand you've lost me.” I stopped her for fear of my mind imploding.
She tittered again, and rose from her seat. “Well I need to get going, I have a letter to write.”
“Pen pal?” I ventured, standing as well.
“Something like that.” She made her way to the front door, and I walked her out.
“Good luck, Twilight”
“Thank you, Guilty.” She took four steps out the door before turning around.
“Oh, I almost forgot to ask… what is your special talent?”
“That, Twilight, is a secret.” I waved goodbye to her as she turned once more toward Ponyville. I was about to close the door when a rather strong gust of wind forced it back open. As I stumbled, I caught glimpse of Twilight. Her tail had been upturned by the gust, Providing me with a absolute perfect view of here tight marehood. The thing that caught my attention however was the small pink wire that connected her opening to a small equally pink remote nestled in her tail.
‘Oh well,’ I concluded, ‘she can keep the vibrator. I’m sure it will be very happy with its new owner.’ I closed the door to my home, and hefted my tired self upstairs. Twilight wasn't the only one in need of a shower. I spoiled myself with a nice, warm, sane shower.
As I write now, nestled back into MY bedroom, laundry done, dinner eaten, and house re-beautified, I find myself feeling rather satisfied with myself. I feel as though I've done a good deed breaking Twilight out of her little shell. I hope she and her stallion get along well.
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Here it is! My First Fanfic! Criticism and comment welcome. Hope you enjoy.
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